“Vulnerability can come in many different flavors. It can be a vulnerability about struggles. But vulnerability is also when you can be funny and have a really unguarded, self-deprecating nature,” Scott says. And what we realized very early on is she’s really, really funny. That was kind of like, ‘Oh, I didn’t know that about her, so I think we definitely have to showcase this woman’s sense of humor.”

One of the film’s repeated themes involves the often-unseen hard work — not to mention the considerable time — it takes to become a success, a win that many often (incorrectly) perceive as an “overnight sensation.”

“You know, it’s a story about dreaming,” Scott says. “She says this line at the beginning, it’s in one of her speeches, but I thought it was so profound:’ If you’re going to be a dreamer, you better be a doer.’ That’s just the point of the whole thing. Nothing is given to you, but if you can dream it, then you should go and do it. So I think it’s really inspirational for anyone else [who’s] chasing their dreams.”

For Wilson, this means constantly working — both when it comes to her present-day activities like touring and other professional commitments, and thinking about what’s coming next. 

“One thing, and I don’t know if this is the case for all musicians, but it was a new thing for me, is to see that she’s on tour constantly. She never stops. She doesn’t sit still. But when she does, she goes, and she starts songwriting the next record,” Scott says. “So she’s banking all these songs, and she’s constantly looking to make the next record. So we did capture a handful of the moments in the process of her looking forward, not just touring past records, but building toward [the next one].” 

According to Scott, no documentary is ever crafted in a straight line, and Keepin’ Country Cool doesn’t tell Wilson’s story that way, either. Instead, she, like those of us watching at home, is really just along for the ride.